HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$340+ Cheap flights from Midland (MAF) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midland to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midland to Caribbean

Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated May 1, 2025.

Round-trip from

$340
(American Airlines)

Popular in

November

Cheapest in

January

Average price

$569
From Midland Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($98 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

Find flight deals from Midland to Caribbean

Cheapest flights from Midland to Caribbean
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/29:03 amMAF - SJU
2 stops14h 02mAmerican Airlines
Sat 9/65:25 pmSJU - MAF
2 stops16h 13mAmerican Airlines
Deal found 4/30$340
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/29:46 amMAF - SJU
1 stop9h 52mUnited Airlines
Sat 9/62:00 pmSJU - MAF
1 stop10h 15mUnited Airlines
Deal found 4/30$410
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/195:00 amMAF - MBJ
1 stop9h 35mAmerican Airlines
Sun 8/172:30 pmMBJ - MAF
2 stops19h 12mAmerican Airlines
Deal found 4/30$550
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/185:35 amMAF - SJU
2 stops12h 10mSouthwest
Sun 9/2110:25 pmSJU - MAF
2 stops12h 30mSouthwest
Deal found 4/29$559
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/174:16 pmMAF - SDQ
2 stops17h 59mAmerican Airlines
Sat 5/246:24 amSDQ - MAF
2 stops18h 28mAmerican Airlines
Deal found 4/29$584
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/285:29 amMAF - MBJ
2 stops10h 01mDelta
Wed 6/42:23 pmMBJ - MAF
2 stops9h 39mDelta
Deal found 4/30$604
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/195:00 amMAF - MBJ
1 stop8h 30mUnited Airlines
Sun 8/172:40 pmMBJ - MAF
1 stop8h 35mUnited Airlines
Deal found 4/30$631

Cheapflights Fare Finder

Customize your flight search to find flights from Midland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 1, 2025.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.

Fly from

Midland

Fly to

Caribbean

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 9/2

9:03 am-12:05 am

2 stops14h 02m

San Juan Luis Munoz Marin Intl

Sat 9/6

5:25 pm-8:38 am

2 stops16h 13m

$340

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 9/2

9:46 am-8:38 pm

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Sat 9/6

2:00 pm-11:15 pm

1 stop10h 15m

$410

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Mon 5/19

5:00 am-2:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Sun 8/17

2:30 pm-9:42 am

2 stops19h 12m

$550

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Thu 9/18

5:35 am-6:45 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Sun 9/21

10:25 pm-9:55 am

2 stops12h 30m

$559

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Sat 5/17

4:16 pm-11:15 am

2 stops17h 59m

Santo Domingo Las Americas

Sat 5/24

6:24 am-11:52 pm

2 stops18h 28m

$584

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Wed 5/28

5:29 am-3:30 pm

2 stops10h 01m

Montego Bay Sangster Intl

Wed 6/4

2:23 pm-12:02 am

2 stops9h 39m

$604

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Mon 5/19

5:00 am-1:30 pm

1 stop8h 30m

Montego Bay Sangster Intl

Sun 8/17

2:40 pm-11:15 pm

1 stop8h 35m

$631

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Best time to book a flight from Midland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Caribbean

What is the cheapest month to book a flight from Midland to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Midland to Caribbean (average of $254). Flying from Midland to Caribbean in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MAF to CB?

Find hourly flight availability from Midland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Midland to Caribbean as you normally would.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated May 1, 2025.
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Caribbean?

    Most people fly from Midland Intl (MAF) if they book a flight from Midland to Caribbean. Midland Intl is conveniently located just 8.2 mi from Midland’s city center.

  • What are the most popular routes from Midland to Caribbean?

    The most popular flight routes from Midland to Caribbean are Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Montego Bay Sangster Intl and Midland Intl - Santo Domingo Las Americas.

  • Can I find deals for flights from Midland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Caribbean.

  • Can I find deals for business class flights from Midland to Caribbean?

    Yes. Cheapflights offers flight deals from Midland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Midland to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Midland to Caribbean (average of $254). Flying from Midland to Caribbean in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to Los Angeles flights
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
George Bush Intcntl to Cancún flights
Dallas/Fort Worth to Cancún flights
Dallas/Fort Worth to Newark flights
Dallas/Fort Worth to Las Vegas flights
Hobby to John F Kennedy Intl flights
Hobby to Las Vegas flights
Hobby to LaGuardia flights
Dallas/Fort Worth to San Francisco flights
Hobby to Seattle flights
Dallas/Fort Worth to Orlando flights
Dallas/Fort Worth to Denver flights
Dallas/Fort Worth to Midway flights
Hobby to Cancún flights
George Bush Intcntl to Las Vegas flights
Hobby to Los Angeles flights
Dallas/Fort Worth to Miami flights
Dallas/Fort Worth to Fort Lauderdale flights
George Bush Intcntl to John F Kennedy Intl flights
Hobby to Newark flights
George Bush Intcntl to Seattle flights
Dallas/Fort Worth to Heathrow flights
Austin to Newark flights
Love Field to LaGuardia flights
George Bush Intcntl to Newark flights
Dallas/Fort Worth to Reagan-National flights
Dallas/Fort Worth to Boston flights
Love Field to Cancún flights
Dallas/Fort Worth to Dulles Intl flights
Dallas/Fort Worth to Cozumel flights
Dallas/Fort Worth to Mexico City flights
Hobby to Denver flights
Dallas/Fort Worth to Charles de Gaulle flights
Austin to Seattle flights
Dallas/Fort Worth to Baltimore flights
George Bush Intcntl to LaGuardia flights
Dallas/Fort Worth to Narita flights
Hobby to Miami flights
George Bush Intcntl to Los Angeles flights
Dallas/Fort Worth to Haneda flights
Dallas/Fort Worth to Burbank flights
Dallas/Fort Worth to Santa Ana flights
Dallas/Fort Worth to Portland flights
Hobby to Orlando flights
Dallas/Fort Worth to Minneapolis flights
Dallas/Fort Worth to Hobby flights

Top 2 airlines flying from Midland to Caribbean

Discover the top 2 airlines that operate flights from Midland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$358Average$738FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$370Average$664FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.